30-Year Playbook

"There is only one thing more painful than learning from experience and that is not learning from experience."

— Archibald MacLeish

I've spent a lot of time recently thinking about the last 30 years of my career and the experiences that have shaped how I lead today. There have been some incredible highs, some pretty significant lows, and plenty of things in between that I probably didn't appreciate at the time. Looking back now, I realize they all mattered.

Every experience has context around it. The company you are working for matters. The people you are surrounded by matter. The maturity of the organization matters. The financial condition of the business matters. Whether the company is growing, struggling, investing, cutting, transforming, or simply trying to survive matters. There is rarely one playbook that works in every situation.

That's an important lesson because it's easy to look backward and decide that something worked or didn't work without considering the circumstances around it. I've seen strategies work incredibly well in one organization and fail in another. I've seen great people struggle because they were in the wrong environment or at the wrong stage of a company's development. I've also seen decisions that looked wrong in the short term turn out to be exactly what a business needed over the long term.

The interesting thing about experience is that you usually don't know you're learning something important while it's happening. You don't go through a difficult period thinking, "I'm going to rely on this experience 10 years from now." You're simply trying to solve the problem in front of you. Sometimes it isn't until years later, when you encounter a similar situation, that you realize how much that previous experience taught you.

That's why I believe so strongly in reps. You need a lot of them, and they need to come in all shapes and sizes. You need to experience success, failure, growth, contraction, great teams, dysfunctional teams, strong balance sheets, financial pressure, good decisions, bad decisions, and decisions where you won't know the answer for years. You need the highest of highs, but you also need some of the lowest of lows.

Those reps eventually turn into something incredibly valuable: pattern recognition.

After enough experiences, you begin to see things developing a little sooner. You recognize pain points before they become major problems. You notice when an organization is trying to move faster than its infrastructure can support. You understand when a people problem is really a process problem, or when a process problem is actually a leadership problem. You become more comfortable making decisions without having perfect information because you've seen enough situations to understand what can happen next.

Experience also gives you something that I probably didn't have enough of earlier in my career: the conviction to say "NO." No to opportunities that look great on paper but don't fit the strategy. No to moving faster simply because everyone wants immediate results. No to adding complexity before the organization is ready for it. No to short-term wins that could create long-term problems. And sometimes, no to your own ideas when the facts tell you that you're wrong.

I find myself relying on those experiences every day right now as we lead our company through a massive transition. We aren't trying to do the impossible, but we are trying to do something difficult. We are building for where we want to be without losing sight of where we are today. This takes patience. It takes experience. It takes trusting people and giving them room to succeed. It takes taking risks while understanding which risks are worth taking. It takes accepting that not every decision will produce an immediate return. Most importantly, it requires looking at the long-term success of the business instead of constantly chasing short-term wins.

There are certainly things I would do differently if I could replay parts of the last 30 years. There are decisions I got wrong, people I probably trusted too much, people I didn't trust enough, opportunities I missed, and situations where I should have moved faster or slower.

But I wouldn't trade those experiences.

The wins gave me confidence. The losses gave me perspective. The difficult situations gave me pattern recognition. And all of those reps have given me a much better understanding of what it actually takes to build and lead a company through change.

Thirty years doesn't mean I have all the answers. Far from it. I'm still learning every day. But I do have a much larger library of experiences to pull from when something happens. I can recognize certain patterns faster, ask better questions, and hopefully make better decisions because I've seen versions of the situation before. That's the value of experience that I probably didn't fully understand when I was younger. You don't collect experiences just to look backward at them. You collect them, often without realizing it, so they're there when you need them most.

TODAY, I'm relying on all 30 years.....